- THE BASE-CATALYZED CYCLIZATION OF 10-OXOCITRAL. SYNTHESIS OF CHRYSOMELIDIAL AND DEHYDROIRIDODIAL
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Base treatment of 10-oxocitral (1) gives chrysomelidial (9) and dehydroiridodial (10), supporting the intermediacy of 1 in the biosynthesis of some iridoid glucosides.Cannizzaro reaction of 9 and 10 affords regioselectively a new iridolactone, 1,2-dehydroisoiridomirmecin (13).
- Bellesia, Franco,Ghelfi, Franco,Pagnoni, Ugo M.,Pinetti, Adriano
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p. 381 - 382
(2007/10/02)
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- FUNCTIONALIZED CYCLOPENTANE DERIVATIVES FROM THE PHOTOADDUCTS OF METHYL 2,4-DIOXOPENTANOATE-OLEFINS: ALTERNATIVE SYNTHESES OF dl-DEHYDROIRIDODIAL AND dl-CHRYSOMELIDIAL
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Functionalized cyclopentane derivatives were prepared by the retro-ozonolysis of methyl 2,6-dioxoheptanoates, which are readily accessible from the photocycloaddition of methyl 2,4-dioxopentanoate with olefins.By this method, 3-isopropenyl-2-methoxycarbonyl-1-methylcyclopentene, a versatile intermediate to iridoid terpenoids, and 1-methoxycarbonyl-2,6,6-trimethylfulvene were synthesized from isoprene.Alternative syntheses of dl-dehydroiridodial and dl-chrysomelidial were accomplished.
- Takeshita, Hitoshi,Hatsui, Toshihide,Kato, Nobuo,Masuda, Takeshi,Tagoshi, Hirotaka
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p. 1153 - 1156
(2007/10/02)
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- TRICYCLO2,8>OCTANONES AS BUILDING BLOCKS IN NATURAL PRODUCTS SYNTHESIS (I). --THE SYNTHESIS OF CHRYSOMELIDIAL--
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The stereocontrolled synthesis of chrysomelidial from 4-methyl-tricyclo2,8>octan-3-one is described.
- Kon, Kenji,Isoe, Sachihiko
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p. 3399 - 3402
(2007/10/02)
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